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Inhibition of the histone demethylase JMJD2E by 3-substituted pyridine 2,4-dicarboxylates

Based on structural analysis of the human 2-oxoglutarate (2OG) dependent JMJD2 histone Nepsilon-methyl lysyl demethylase family, 3-substituted pyridine 2,4-dicarboxylic acids were identified as potential inhibitors with possible selectivity over other human 2OG oxygenases. Microwave-assisted palladium-catalysed cross coupling methodology was developed to install a diverse set of substituents on the sterically demanding C-3 position of a pyridine 2,4-dicarboxylate scaffold. The subsequently prepared di-acids were tested for in vitro inhibition of the histone demethylase JMJD2E and another human 2OG oxygenase, prolyl-hydroxylase domain isoform 2 (PHD2, EGLN1). A subset of substitution patterns yielded inhibitors with selectivity for JMJD2E over PHD2, demonstrating that structure-based inhibitor design can enable selective inhibition of histone demethylases over related human 2OG oxygenases.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Multifunctional isoquinoline-oxazoline ligands of chemical and biological importance

Multifunctional isoquinoline-oxazolines (MIQOXs) were conceived and synthesized from commercially available chiral amino acids. The multifunctional role of MIQOXs was demonstrated by Pd-catalyzed highly enantioselective addition of arylboronic acids to nitrostyrenes, and by the discovery of novel antifungal candidates.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Qualitative analysis of trace constituents by ion mobility increment spectrometer

Ion mobility increment spectrometry (IMIS) is a high sensitive selective ionization technology for detection and identification of ultra-trace constituents, including toxic compounds, CW-agents, drugs and explosives in ambient air or liquid sample. Like an ion mobility spectrometry (IMS), this technology rests on sampling air containing a mixture of trace constituents, its ionization, spatial separation of produced ions and separated ions detection. Unlike IMS, ions of different types in IMIS are separated by ion mobility increment, alpha. Value alpha, is a function of the parameters: electric field strength and form, atmospheric pressure. To exclude the influence of these parameters on an alpha, the method of explosives identification by a standard compound was suggested. As a standard compound iodine was used. The relationship among the mobility coefficient increments equal to the relationship among the compensation voltage alpha i/alphaiodine = Ui/Uiodine is determined, where i are ions of 1,3-dinitrobenzene, 1,3,5-trinitrobenzene, p-mononitrotoluene, 2,4-dinitrotoluene and 2,4,6-trinitrotoluene This relationship is practically independent of the above mentioned parameters in the range 25 < E/N < 90 Td. The limits of the relative error of this relationship are determined both from spectra of individual compounds and nitrocompound-iodine mixtures. We¡¯ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 108-47-4, and how the biochemistry of the body works.Synthetic Route of 108-47-4

Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Solid phase assisted synthesis of HIV-1 inhibitors. Expedient entry to unsymmetrical substitution of a C2 symmetric template

A solid phase synthesis has been developed leading up to unsymmetrical HIV-1 protease inhibitors that are not readily available by conventional solution phase chemistry (18a-g). To prepare these compounds the hydroxyl group of (1s,2r)-(-)-cis-1-phthalimido-2-indanol (3) was coupled to a Merrifield resin via a dihydropyrane linker. Cleavage of the phthalimido protecting group and reaction of the liberated amine with the bis-activated symmetrical diacid 15 resulted in the resin bound amide 16. Coupling of 16 with amino acids and amines followed by hydrolysis produced the desired unsymmetrical products 18a-g from which potent HIV-1 protease inhibitors were identified, e.g., 18e (k(i) = 0.1 nM), 18a (k(i) = 0.2 nM) and 18c (k(i) = 2 nM).

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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The kinetics of the decompositions of the proton bound dimers of 1,4-dimethylpyridine and dimethyl methylphosphonate from atmospheric pressure ion mobility spectra

The rate constants for the dissociations, A2H+ ? AH+ + A, of the symmetrical proton bound dimers of 2,4-dimethylpyridine and dimethyl methylphosphonate have been determined using an ion mobility spectrometer operating with air as drift gas at ambient pressure. Reaction time was varied by varying the drift electric field. The rate constants were derived from the mobility spectra by determining the rate at which ions decomposed in the drift region. Arrhenius plots with a drift gas containing water vapor at 5 ppmv gave the following activation energies and pre-exponential factors: 2,4-dimethylpyridine, 94 ¡À 2 kJ mol-1, log A (s-1) = 15.9 ¡À 0.4; dimethyl methylphosphonate, 127 ¡À 3 kJ mol-1, log A (s-1) = 15.6 ¡À 0.3. The enthalpy changes for the decompositions calculated from the activation energies are in accord with literature values for symmetrical proton bound dimers of oxygen and nitrogen bases. The results for dimethyl methylphosphonate were obtained over the temperature range 478-497 K and are practically independent of water concentration (5-2000 ppmv). The activation energy for 2,4-dimethylpyridine, obtained over the temperature range 340-359 K, decreased to 31 kJ mol-1 in the presence of 2.0 ¡Á 103 ppmv of water. At the low temperature, a displacement reaction involving water may account for the decrease. The reduced mobilities of the protonated molecules and the proton bound dimers have been determined over a wide temperature range. While the values for the dimers are essentially independent of the water concentration in the drift gas, those of the protonated molecules show a strong dependence.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Scientific opinion on flavouring group evaluation 77, revision 3 (FGE.77Rev3): consideration of pyridine, pyrrole and quinoline derivatives evaluated by JECFA (63rd meeting) structurally related to pyridine, pyrrole, indole and quinoline derivatives evaluated by EFSA in FGE.24Rev2

The Panel?on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the EFSA was requested to consider evaluations of flavouring substances assessed since 2000 by the Joint FAO/WHO Expert Committee on Food Additives (JECFA) and to decide whether further evaluation is necessary, as laid down in Commission Regulation (EC) No 1565/2000. The present consideration concerns a group of 22 pyridine, pyrrole and quinoline derivatives evaluated by JECFA (63rd meeting). The revision of this consideration is made since additional genotoxicity data have become available for 6-methylquinoline [FL-no: 14.042]. The genotoxicity data available rule out the concern with respect to genotoxicity and accordingly the substance is evaluated through the Procedure. For all 22 substances [FL-no: 13.134, 14.001, 14.004, 14.007, 14.030, 14.038, 14.039, 14.041, 14.042, 14.045, 14.046, 14.047, 14.058, 14.059, 14.060, 14.061, 14.065, 14.066, 14.068, 14.071, 14.072 and 14.164] considered in this Flavouring Group Evaluation (FGE), the Panel?agrees with the JECFA conclusion, ?No safety concern at estimated levels of intake as flavouring substances? based on the Maximised Survey-derived Daily Intake (MSDI) approach. Besides the safety assessment of these flavouring substances, the specifications for the materials of commerce have also been evaluated, and the information is considered adequate for all the substances. For the following substances [FL-no: 13.134, 14.001, 14.030, 14.041, 14.042, 14.058, 14.072], the Industry has submitted use levels for normal and maximum use. For the remaining 15 substances, use levels are needed to calculate the modified Theoretical Added Maximum Daily Intakes (mTAMDIs) in order to identify those flavouring substances that need more refined exposure assessment and to finalise the evaluation.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Highly stereoselective reduction of alpha-keto esters: Utility of cis-1-arylsulfonamido-2-indanols as chiral auxiliaries

The reduction of alpha-keto esters bearing cis-1-arylsulfonamide-2-indanol derivatives proceeded with high diastereoselectivities providing the corresponding alpha-hydroxy esters in excellent yields. The chiral auxiliary group is removed under mild basic conditions and recovered.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Metabolic profiling of human blood by high-resolution ion mobility mass spectrometry (IM-MS)

A high-resolution ion mobility time-of-flight mass spectrometer with electrospray ionization source (ESI-IM-MS) was evaluated as an analytical method for rapid analysis of complex biological samples such as human blood metabolome. The hybrid instrument (IM-MS) provided an average ion mobility resolving power of ?90 and a mass resolution of ?1500 (at m/. z 100). A few muL of whole blood was extracted with methanol, centrifuged and infused into the IM-MS via an electrospray ionization source. Upon IM-MS profiling of the human blood metabolome approximately 1100 metabolite ions were detected and 300 isomeric metabolites separated in short analyses time (30. min). Estimated concentration of the metabolites ranged from the low micromolar to the low nanomolar level. Various classes of metabolites (amino acids, organic acids, fatty acids, carbohydrates, purines and pyrimidines, etc.) were found to form characteristic mobility-mass correlation curves (MMCCs) that aided in metabolite identification. Peaks corresponding to various sterol derivatives, estrogen derivatives, phosphocholines, prostaglandins, and cholesterol derivatives detected in the blood extract were found to occupy characteristic two-dimensional IM-MS space. Low abundance metabolite peaks that can be lost in MS random noise were resolved from noise peaks by differentiation in mobility space. In addition, the peak capacity of MS increased sixfold by coupling IMS prior to MS analysis.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Ruthenium-NHC-Catalyzed asymmetric hydrogenation of indolizines: Access to indolizidine alkaloids

Crossing N-bridges! A ruthenium/N-heterocyclic carbene (NHC) complex serves as the catalyst for the high-yielding and completely regioselective and asymmetric hydrogenation of substituted indolizines and 1,2,3-triazolo-[1,5-a] pyridines. This method should provide ready access to bicyclic products bearing an N-bridgehead, a motif appearing in 25-30 % of all naturally occurring alkaloids. Copyright

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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2-Methylpyridinium Salts as 1,4-Dinucleophiles. II. Westphal Condensation with Substituted Pyridinium Substrates

Condensation of alpha-methylpyridinium, quinolinium and isoquinolinium salts with 1,2-dicarbonyls in the presence of base, yielded quinolizinium derivatives.In an analogous process, alpha-benzyl derivatives produced 2,3-dihydroindolizin-2-ones by intramolecular cyclisation.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis